TW202448B - - Google Patents

Download PDF

Info

Publication number: TW202448B
Authority: TW; Taiwan
Prior art keywords: group; alkyl; substituted; formula; alkoxy
Prior art date: 1991-06-05

Application number

TW081104270A

Other languages

English (en)

Chinese (zh)

Original Assignee

Sanofi Elf

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-06-05

Filing date

1992-06-01

Publication date

1993-03-21

1992-06-01 Application filed by Sanofi Elf filed Critical Sanofi Elf

1993-03-21 Application granted granted Critical

1993-03-21 Publication of TW202448B publication Critical patent/TW202448B/zh

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 66
150000001875 compounds Chemical class 0.000 claims abstract description 64
125000003545 alkoxy group Chemical group 0.000 claims abstract description 27
125000005843 halogen group Chemical group 0.000 claims abstract description 17
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
125000001424 substituent group Chemical group 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
125000005842 heteroatom Chemical group 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 3
-1 hexahydropyridinyl Chemical group 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
125000001041 indolyl group Chemical group 0.000 claims description 11
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
238000011049 filling Methods 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000007789 gas Substances 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
108010052343 Gastrins Proteins 0.000 claims description 5
AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 5
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical group N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
238000010511 deprotection reaction Methods 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
229950003476 aminothiazole Drugs 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
125000005968 oxazolinyl group Chemical group 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
230000028327 secretion Effects 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000005309 thioalkoxy group Chemical group 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
102100021022 Gastrin Human genes 0.000 claims 3
239000004382 Amylase Substances 0.000 claims 2
102000013142 Amylases Human genes 0.000 claims 2
108010065511 Amylases Proteins 0.000 claims 2
235000019418 amylase Nutrition 0.000 claims 2
125000000743 hydrocarbylene group Chemical group 0.000 claims 2
125000002971 oxazolyl group Chemical group 0.000 claims 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
210000002784 stomach Anatomy 0.000 claims 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 1
101100476210 Caenorhabditis elegans rnt-1 gene Proteins 0.000 claims 1
241000700199 Cavia porcellus Species 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
241000699670 Mus sp. Species 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
210000001156 gastric mucosa Anatomy 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
238000001727 in vivo Methods 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
230000024717 negative regulation of secretion Effects 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 12
229910052760 oxygen Inorganic materials 0.000 abstract description 5
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000004103 aminoalkyl group Chemical group 0.000 abstract 1
125000005242 carbamoyl alkyl group Chemical group 0.000 abstract 1
125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 abstract 1
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 46
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 31
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
230000033228 biological regulation Effects 0.000 description 20
239000012074 organic phase Substances 0.000 description 17
150000002576 ketones Chemical class 0.000 description 16
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
240000004808 Saccharomyces cerevisiae Species 0.000 description 13
239000012071 phase Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
238000001914 filtration Methods 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
230000027455 binding Effects 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
238000010908 decantation Methods 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
238000012360 testing method Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
108010086019 Secretin Proteins 0.000 description 4
102100037505 Secretin Human genes 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
230000002079 cooperative effect Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
229960002101 secretin Drugs 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
150000003557 thiazoles Chemical class 0.000 description 4
238000005406 washing Methods 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
239000010931 gold Substances 0.000 description 3
229910052737 gold Inorganic materials 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000010985 leather Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical class NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 description 2
CGZDWVZMOMDGBN-UHFFFAOYSA-N 2-Ethylthiazole Chemical compound CCC1=NC=CS1 CGZDWVZMOMDGBN-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
JMCITVCSEVUIAW-UHFFFAOYSA-N 5-methoxy-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1OC JMCITVCSEVUIAW-UHFFFAOYSA-N 0.000 description 2
101800001982 Cholecystokinin Proteins 0.000 description 2
102100025841 Cholecystokinin Human genes 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
229910052692 Dysprosium Inorganic materials 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
102400000921 Gastrin Human genes 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
108090000787 Subtilisin Proteins 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
239000002775 capsule Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
125000005518 carboxamido group Chemical group 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
229940107137 cholecystokinin Drugs 0.000 description 2
239000003754 cholecystokinin receptor blocking agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004040 coloring Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
210000004907 gland Anatomy 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000009434 installation Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000010647 peptide synthesis reaction Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
NYIGEYYREVRXES-UHFFFAOYSA-N pyrazol-1-amine Chemical group NN1C=CC=N1 NYIGEYYREVRXES-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
238000012552 review Methods 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
239000013049 sediment Substances 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
229910052712 strontium Inorganic materials 0.000 description 2
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
230000009278 visceral effect Effects 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical group CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
RCSKFKICHQAKEZ-UHFFFAOYSA-N 1-ethenylindole Chemical compound C1=CC=C2N(C=C)C=CC2=C1 RCSKFKICHQAKEZ-UHFFFAOYSA-N 0.000 description 1
FPVIIOSXSGECQO-UHFFFAOYSA-N 1-ethylindole-2-carboxylic acid Chemical compound C1=CC=C2N(CC)C(C(O)=O)=CC2=C1 FPVIIOSXSGECQO-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
DVIIMIPZKGGFFF-UHFFFAOYSA-N 2-(2-amino-4-phenyl-1,3-thiazol-5-yl)ethanol Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1CCO DVIIMIPZKGGFFF-UHFFFAOYSA-N 0.000 description 1
LQHZBBOWHMBQLQ-UHFFFAOYSA-N 2-ethyl-4-phenyl-1,3-thiazole Chemical compound S1C(CC)=NC(C=2C=CC=CC=2)=C1 LQHZBBOWHMBQLQ-UHFFFAOYSA-N 0.000 description 1
VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
OTCFHGIJKQWKTL-UHFFFAOYSA-N 5-(2-aminoethyl)-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1CCN OTCFHGIJKQWKTL-UHFFFAOYSA-N 0.000 description 1
YUMHQQUMURQNOP-UHFFFAOYSA-N 5-benzyl-4-(2,4-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound COC1=CC(OC)=CC=C1C1=C(CC=2C=CC=CC=2)SC(N)=N1 YUMHQQUMURQNOP-UHFFFAOYSA-N 0.000 description 1
DWUPYMSVAPQXMS-UHFFFAOYSA-N 5-bromo-1,3-thiazole Chemical compound BrC1=CN=CS1 DWUPYMSVAPQXMS-UHFFFAOYSA-N 0.000 description 1
229920003026 Acene Polymers 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
102000040350 B family Human genes 0.000 description 1
108091072128 B family Proteins 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
206010006100 Bradykinesia Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
COMAFKOFECWALP-UHFFFAOYSA-N CCSC1=C2C=CC3=CC=CC4=C3C2=C(C=C4)C=C1 Chemical compound CCSC1=C2C=CC3=CC=CC4=C3C2=C(C=C4)C=C1 COMAFKOFECWALP-UHFFFAOYSA-N 0.000 description 1
PVGCVHTVWDPYDC-UHFFFAOYSA-N CNC(C(=O)C1=CC=CC=C1)Br Chemical compound CNC(C(=O)C1=CC=CC=C1)Br PVGCVHTVWDPYDC-UHFFFAOYSA-N 0.000 description 1
206010058019 Cancer Pain Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000000668 Chronic Pancreatitis Diseases 0.000 description 1
244000301850 Cupressus sempervirens Species 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
210000000712 G cell Anatomy 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000162682 Heterogen Species 0.000 description 1
208000006083 Hypokinesia Diseases 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
WLHBRQYVZLNQFE-UHFFFAOYSA-N O[S+]1C2=CC=CC=C2N=C1 Chemical compound O[S+]1C2=CC=CC=C2N=C1 WLHBRQYVZLNQFE-UHFFFAOYSA-N 0.000 description 1
239000008896 Opium Substances 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
244000131316 Panax pseudoginseng Species 0.000 description 1
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
206010033647 Pancreatitis acute Diseases 0.000 description 1
206010033649 Pancreatitis chronic Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
240000005481 Salvia hispanica Species 0.000 description 1
235000001498 Salvia hispanica Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000270666 Testudines Species 0.000 description 1
241001061127 Thione Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
244000126002 Ziziphus vulgaris Species 0.000 description 1
201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
239000012190 activator Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
201000003229 acute pancreatitis Diseases 0.000 description 1
JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
125000006294 amino alkylene group Chemical group 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
235000021229 appetite regulation Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
238000011001 backwashing Methods 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
GBVAGZMJJSANDQ-UHFFFAOYSA-N benzyl 1h-indole-2-carboxylate Chemical compound C=1C2=CC=CC=C2NC=1C(=O)OCC1=CC=CC=C1 GBVAGZMJJSANDQ-UHFFFAOYSA-N 0.000 description 1
210000000013 bile duct Anatomy 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011449 brick Substances 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
238000009933 burial Methods 0.000 description 1
239000001273 butane Substances 0.000 description 1
ZTWDCZMOZWATCE-UHFFFAOYSA-N butane;carboxy hydrogen carbonate Chemical compound CCCC.OC(=O)OC(O)=O ZTWDCZMOZWATCE-UHFFFAOYSA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000014167 chia Nutrition 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
230000001427 coherent effect Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
HYMMVSZYUJTURQ-UHFFFAOYSA-N ethyl 2-(1h-indole-2-carbonylamino)-4-phenyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(NC(=O)C=2NC3=CC=CC=C3C=2)=NC=1C1=CC=CC=C1 HYMMVSZYUJTURQ-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
201000000052 gastrinoma Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000003721 gunpowder Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
230000002766 immunoenhancing effect Effects 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
229910052743 krypton Inorganic materials 0.000 description 1
DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical group [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VXHYMZHKGHLQNO-UHFFFAOYSA-N methanesulfonic acid;toluene Chemical class CS(O)(=O)=O.CC1=CC=CC=C1 VXHYMZHKGHLQNO-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
238000005065 mining Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
229960001027 opium Drugs 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000012856 packing Methods 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
208000024335 physical disease Diseases 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
238000005554 pickling Methods 0.000 description 1
QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
XWNXEWLCHSLQOI-UHFFFAOYSA-K trisodium;triacetate Chemical compound [Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O XWNXEWLCHSLQOI-UHFFFAOYSA-K 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Rheumatology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

TW081104270A 1991-06-05 1992-06-01 TW202448B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9106814A FR2677356B1 (fr)	1991-06-05	1991-06-05	Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant.

Publications (1)

Publication Number	Publication Date
TW202448B true TW202448B (de)	1993-03-21

Family

ID=9413505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW081104270A TW202448B (de)	1991-06-05	1992-06-01

Country Status (23)

Country	Link
US (2)	US5314889A (de)
EP (1)	EP0518731B1 (de)
JP (1)	JP3199451B2 (de)
KR (1)	KR100222309B1 (de)
AT (1)	ATE170186T1 (de)
AU (1)	AU650754B2 (de)
BR (2)	BR9202156A (de)
CA (1)	CA2070526A1 (de)
CZ (1)	CZ289003B6 (de)
DE (1)	DE69226729T2 (de)
ES (1)	ES2121575T3 (de)
FI (1)	FI922589A7 (de)
FR (1)	FR2677356B1 (de)
HU (1)	HU221312B1 (de)
IE (1)	IE921814A1 (de)
IL (1)	IL102004A (de)
MX (1)	MX9202662A (de)
NO (1)	NO300135B1 (de)
NZ (1)	NZ243009A (de)
RU (1)	RU2059637C1 (de)
TW (1)	TW202448B (de)
UA (1)	UA26899C2 (de)
ZA (1)	ZA923981B (de)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4303676A1 (de) *	1993-02-09	1994-08-11	Bayer Ag	1-Aryltriazolin(thi)one
FR2701708B1 (fr) *	1993-02-19	1995-05-19	Sanofi Elf	Dérivés de 2-amido-4-phénylthiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament.
FR2703995B1 (fr) *	1993-04-16	1995-07-21	Sanofi Elf	5-acylamino 1,2,4-thiadiazoles, leur preparation et compositions pharmaceutiques en contenant.
WO1995032963A1 (en) *	1994-06-01	1995-12-07	Yoshitomi Pharmaceutical Industries, Ltd.	Thienylazole compound and thienotriazolodiazepine compound
MX9604483A (es) *	1994-09-08	1998-02-28	Jean-Francois Rossignol	Derivados de benzamida, composiciones que contienen dicho derivado y uso de las mismas.
CN1102593C (zh) *	1996-06-27	2003-03-05	詹森药业有限公司	N－[4－(杂芳基甲基)苯基]－杂芳基胺类化合物
AU6659298A (en)	1997-02-18	1998-09-08	Thomas Jefferson University	Compositions that bind to pancreatic cancer cells and methods of using the same
CO4970713A1 (es)	1997-09-19	2000-11-07	Sanofi Synthelabo	Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen
FR2768737B1 (fr) *	1997-09-19	2000-05-19	Sanofi Sa	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
GB0028383D0 (en) *	2000-11-21	2001-01-03	Novartis Ag	Organic compounds
EP1361220A4 (de) *	2001-01-26	2005-09-07	Shionogi & Co	Cyclische verbindungen mit thrombopoietinrezeporagonismus
JPWO2002062775A1 (ja) *	2001-02-02	2004-06-10	山之内製薬株式会社	２−アシルアミノチアゾール誘導体又はその塩
JP4120586B2 (ja) *	2002-01-18	2008-07-16	アステラス製薬株式会社	２−アシルアミノチアゾール誘導体又はその塩
US20030225054A1 (en) *	2002-06-03	2003-12-04	Jingwu Duan	Combined use of tace inhibitors and COX2 inhibitors as anti-inflammatory agents
FR2854158B1 (fr) *	2003-04-25	2006-11-17	Sanofi Synthelabo	Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique
MXPA06000441A (es) *	2003-07-17	2006-04-05	Astellas Pharma Inc	Derivado de 2-acilaminotiazole o sal del mismo.
TWI336697B (en) *	2003-09-19	2011-02-01	Solvay Pharm Bv	Thiazole derivatives as cannabinoid receptor modulators
WO2005058887A1 (en) *	2003-12-08	2005-06-30	F. Hoffmann-La Roche Ag	Novel thiazole derivates
JP4638355B2 (ja) *	2003-12-26	2011-02-23	協和発酵キリン株式会社	チアゾール誘導体
GB0401336D0 (en) *	2004-01-21	2004-02-25	Novartis Ag	Organic compounds
EP3461813A1 (de)	2004-05-23	2019-04-03	Gerard M. Housey	Theramuteinmodulatoren
FR2872813B1 (fr) *	2004-07-09	2007-01-19	Sanofi Synthelabo	Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique
CA2575466A1 (en) *	2004-08-13	2006-02-23	Genentech, Inc.	Thiazole based inhibitors of atp-utilizing enzymes
FR2876692B1 (fr) *	2004-10-19	2007-02-23	Sanofi Aventis Sa	Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique
JP4774995B2 (ja) *	2005-01-12	2011-09-21	アステラス製薬株式会社	アシルアミノチアゾール誘導体を有効成分とする医薬組成物
CA2618646A1 (en) *	2005-06-03	2007-11-15	Xenon Pharmaceuticals Inc.	Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors
EP1894930A4 (de) *	2005-06-23	2010-06-23	Kyowa Hakko Kirin Co Ltd	Thiazolderivat
US7928098B2 (en)	2005-08-02	2011-04-19	Kyowa Hakko Kirin Co., Ltd.	Therapeutic and/or preventive agents for a sleep disorder
WO2007054783A2 (en) *	2005-11-08	2007-05-18	Astellas Pharma Inc.	Compositions and methods for treating thrombocytopenia
FR2895989B1 (fr) *	2006-01-06	2010-04-30	Sanofi Aventis	Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique
US8455658B2 (en) *	2006-01-25	2013-06-04	Synta Pharmaceuticals Corp.	Thiazole and thiadiazole compounds for inflammation and immune-related uses
CN101096363B (zh) *	2006-06-27	2011-05-11	中国人民解放军军事医学科学院毒物药物研究所	2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途
US20080039475A1 (en) *	2006-08-08	2008-02-14	Akarx, Inc.	Compositions and methods for increasing blood platelet levels in humans
US20110052643A1 (en) *	2008-01-07	2011-03-03	Synta Pharmaceuticals Corp.	Compounds for inflammation and immune-related uses
MX2010010659A (es) *	2008-03-31	2010-10-26	Genentech Inc	Compuestos de benzopirano y benzoxepina, inhibidores de fosfoinoinositida 3-cinasas y metodos para utilizarlos.
JP2013501811A (ja) *	2009-08-14	2013-01-17	エーザイインコーポレーテッド	血小板産生を刺激するためのｅ５５０１の使用
US8263633B2 (en)	2009-09-28	2012-09-11	F. Hoffman-La Roche Ag	Benzoxepin PI3K inhibitor compounds and methods of use
MY160064A (en)	2009-09-28	2017-02-15	Hoffmann La Roche	Benzoxazepin pi3k inhibitor compounds and methods of use
KR101609856B1 (ko) *	2010-03-17	2016-04-07	타이벡스 세라피틱스 코포레이션	Ｈｅｃ１ 활성의 조절인자 및 이의 방법
US9090628B2 (en)	2011-03-21	2015-07-28	Genentech, Inc.	Benzoxazepin compounds selective for PI3K P110 delta and methods of use
US9034866B2 (en)	2012-02-17	2015-05-19	Genentech, Inc.	Tricyclic compounds and methods of use therefor
WO2020051424A1 (en)	2018-09-07	2020-03-12	Pic Therapeutics	Eif4e inhibitors and uses thereof
TW202146393A (zh)	2020-03-03	2021-12-16	美商皮克醫療公司	Eif4e抑制劑及其用途
US12459131B2 (en)	2021-05-06	2025-11-04	Mitsubishi Electric Corporation	Picking system
US12157732B2 (en)	2021-08-25	2024-12-03	PIC Therapeutics, Inc.	eIF4E inhibitors and uses thereof
CA3229560A1 (en)	2021-08-25	2023-03-02	Christopher L. Vandeusen	Eif4e inhibitors and uses thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3210368A (en) *	1964-09-29	1965-10-05	Ciba Geigy Corp	Certain 2-amino-4-aryl-5-n, n-disubstituted amino-lower alkyl-thiazole compounds
EP0208510B1 (de) *	1985-07-09	1991-09-11	Pfizer Inc.	Substituierte Oxindol-3-carboxamine als entzündungshemmendes und schmerzstillendes Mittel
DE3705934A1 (de) *	1987-02-25	1988-09-08	Nattermann A & Cie	Indolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4971978A (en) *	1987-09-21	1990-11-20	Nadzan Alex M	Derivatives of D-glutamic acid and D-aspartic acid
US4992437A (en) *	1987-12-22	1991-02-12	Yoshitomi Pharmaceutical Industries, Ltd.	Thienodiazepine compounds and their pharmaceutical use
IE68593B1 (en) *	1989-12-06	1996-06-26	Sanofi Sa	Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them

1991
- 1991-06-05 FR FR9106814A patent/FR2677356B1/fr not_active Expired - Fee Related
1992
- 1992-05-26 IL IL102004A patent/IL102004A/xx not_active IP Right Cessation
- 1992-05-28 AU AU17279/92A patent/AU650754B2/en not_active Ceased
- 1992-05-29 US US07/889,910 patent/US5314889A/en not_active Expired - Fee Related
- 1992-06-01 TW TW081104270A patent/TW202448B/zh active
- 1992-06-01 ZA ZA923981A patent/ZA923981B/xx unknown
- 1992-06-03 DE DE69226729T patent/DE69226729T2/de not_active Expired - Fee Related
- 1992-06-03 NZ NZ243009A patent/NZ243009A/en unknown
- 1992-06-03 AT AT92401518T patent/ATE170186T1/de not_active IP Right Cessation
- 1992-06-03 ES ES92401518T patent/ES2121575T3/es not_active Expired - Lifetime
- 1992-06-03 EP EP92401518A patent/EP0518731B1/de not_active Expired - Lifetime
- 1992-06-04 NO NO922215A patent/NO300135B1/no not_active IP Right Cessation
- 1992-06-04 FI FI922589A patent/FI922589A7/fi not_active Application Discontinuation
- 1992-06-04 RU SU5011874/04A patent/RU2059637C1/ru not_active IP Right Cessation
- 1992-06-04 MX MX9202662A patent/MX9202662A/es not_active IP Right Cessation
- 1992-06-04 CA CA002070526A patent/CA2070526A1/en not_active Abandoned
- 1992-06-04 JP JP14415092A patent/JP3199451B2/ja not_active Expired - Fee Related
- 1992-06-04 HU HU9201870A patent/HU221312B1/hu not_active IP Right Cessation
- 1992-06-04 CZ CS19921693A patent/CZ289003B6/cs not_active IP Right Cessation
- 1992-06-05 KR KR1019920009859A patent/KR100222309B1/ko not_active Expired - Fee Related
- 1992-06-05 BR BR929202156A patent/BR9202156A/pt not_active Application Discontinuation
- 1992-07-01 IE IE181492A patent/IE921814A1/en not_active IP Right Cessation
1993
- 1993-06-15 UA UA93002939A patent/UA26899C2/uk unknown
1994
- 1994-03-03 US US08/205,408 patent/US5380736A/en not_active Expired - Fee Related
1997
- 1997-05-12 BR BR1100786-9A patent/BR1100786A/pt active IP Right Grant

Also Published As

Publication number	Publication date
HK1012397A1 (en)	1999-07-30
FR2677356A1 (fr)	1992-12-11
CA2070526A1 (en)	1992-12-06
UA26899C2 (uk)	1999-12-29
DE69226729T2 (de)	1999-05-06
AU650754B2 (en)	1994-06-30
RU2059637C1 (ru)	1996-05-10
HU221312B1 (en)	2002-09-28
IE921814A1 (en)	1992-12-16
IL102004A0 (en)	1992-12-30
BR1100786A (pt)	2000-03-14
NO300135B1 (no)	1997-04-14
HUT75870A (en)	1997-05-28
EP0518731A1 (de)	1992-12-16
MX9202662A (es)	1992-12-31
NZ243009A (en)	1995-05-26
DE69226729D1 (de)	1998-10-01
JPH05155871A (ja)	1993-06-22
IL102004A (en)	1997-04-15
FR2677356B1 (fr)	1995-03-17
US5380736A (en)	1995-01-10
FI922589A0 (fi)	1992-06-04
NO922215L (no)	1992-12-07
AU1727992A (en)	1992-12-10
FI922589A7 (fi)	1992-12-06
EP0518731B1 (de)	1998-08-26
CZ289003B6 (cs)	2001-10-17
ES2121575T3 (es)	1998-12-01
ATE170186T1 (de)	1998-09-15
NO922215D0 (no)	1992-06-04
CS169392A3 (en)	1992-12-16
KR930000492A (ko)	1993-01-15
BR9202156A (pt)	1993-02-02
KR100222309B1 (ko)	1999-10-01
US5314889A (en)	1994-05-24
JP3199451B2 (ja)	2001-08-20
HU9201870D0 (en)	1992-08-28
ZA923981B (en)	1993-12-01

Publication	Publication Date	Title
TW202448B (de)	1993-03-21
CN101106990B (zh)	2010-12-08	用作蛋白激酶抑制剂的化合物和组合物
US7863279B2 (en)	2011-01-04	Triazolopyridine carboxamide derivatives and triazolopyrimidine carboxamide derivatives, preparation thereof and therapeutic use thereof
TW461889B (en)	2001-11-01	1H-pyrido[3,4-b]indole-4-carboxamide derivatives, their preparation and their application in therapeutics
US20070049558A1 (en)	2007-03-01	New Spirotricyclic Derivatives and Their Use as Phosphodiesterase-7 Inhibitors
CN102216300B (zh)	2014-10-22	作为蛋白激酶抑制剂的化合物和组合物
CN101291938A (zh)	2008-10-22	作为蛋白激酶抑制剂的化合物和组合物
US20070021405A1 (en)	2007-01-25	Aryl- and heteroarylpiperidinecarboxylate-derivatives methods for their preparation and use thereof as fatty acid amido hydrolase enzyme inhibitors
KR20090080567A (ko)	2009-07-24	간 카르니틴 팔미토일 전이효소(ｌ-ｃｐｔｌ)로서 설폰아마이드 유도체
AU2010247212B2 (en)	2015-07-16	5-membered heterocyclic compound cyclopenta[c]pyrrolylalkylcarbamate derivatives, preparation thereof, and therapeutic use thereof
JP2009507884A (ja)	2009-02-26	肝カルニチンパルミトイルトランスフェラーゼのインヒビターとして有用な新規ヘテロ二環式誘導体
US4210648A (en)	1980-07-01	II-Aminoacyl-5,11-dihydro-6H-pyrido(2,3-B) (1,4)benzodiazepin-6-ones and salts thereof
WO2011001931A1 (ja)	2011-01-06	新規オキサジアゾール誘導体
TW295584B (de)	1997-01-11
JPS63264481A (ja)	1988-11-01	新ピペリジン類、これらの化合物を含む薬剤組成物およびそれらを製造する方法
TW502005B (en)	2002-09-11	5-aryl-3-(8-azabicyclo[3.2.1]oct-3-yl)-1,3,4-oxadiazol-2(3H)-one derivatives, their preparation and their therapeutic application in the treatment and prevention of disorders related to 5-HT4 and/or H3 receptors
CA2175498C (en)	2005-07-26	Phenylindole compounds
CA1321996C (en)	1993-09-07	Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds
JPH0788357B2 (ja)	1995-09-27	ピペラジン化合物
US5367078A (en)	1994-11-22	3-oxadiazolyl-1,6-naphthyridine derivatives
JP2014073982A (ja)	2014-04-24	新規ベンズイミダゾール誘導体からなる医薬
TW206230B (de)	1993-05-21
JPH0232074A (ja)	1990-02-01	新規縮合ジアゼピノン類、それらを製造する方法及びこれらの化合物を含有する医薬組成物
JPH06116273A (ja)	1994-04-26	三環系化合物
TW205040B (de)	1993-05-01